Electrochemistry and Electrogenerated Chemiluminescence of 3,6-Di(spirobifluorene)-N-phenylcarbazole
Resource
Journal of the American Chemical Society 130 (2): 634-639
Journal
Journal of the American Chemical Society
Journal Volume
130
Journal Issue
2
Pages
634-639
Date Issued
2008
Date
2008
Author(s)
Abstract
We report here the electrochemistry, luminescence, and electrogenerated chemiluminescence (ECL) of 3,6-dispirobifluorene-N-phenylcarbazole (DSBFNPC). DSBFNPC contains two spirobifluorene groups covalently attached to the N-phenylcarbazole core. The optimized geometry as determined from semiempirical MNDO calculations shows that the phenyl group is twisted 89° from the plane of central carbazole, indicating a lack of electron delocalization between these groups. However, the two fluorene rings of each spirobifluorene group are twisted 58° relative to each other and two spirobifluorene groups are twisted 64° from the N-phenylcarbazole ring, suggesting some charge derealization among these groups. The cyclic voltammetry of this compound shows two reversible oxidation waves (assigned to the formation of the cation and dication) and a two-electron reduction wave that becomes reversible at higher scan rates (assigned to formation of anion). Digital simulations were carried out to obtain details of the electrochemical processes, and electrochemical behavior was compared to that of phenylcarbazole (PC). Upon cycling between the oxidation and reduction waves, ECL is produced by radical ion annihilation. The photophysical properties of DSBFNPC show a strong resemblance to the parent compound, PC, and the ECL spectrum produced via radical ion annihilation shows good agreement with the fluorescence emission spectrum of DSBFNPC. © 2008 American Chemical Society.
SDGs
Type
journal article
File(s)![Thumbnail Image]()
Loading...
Name
37.pdf
Size
141.92 KB
Format
Adobe PDF
Checksum
(MD5):c7e9bc7f6fc9c49a99109449baa3ff21